Purple subphthalocyanine-phthalocyanine dyad: Synthesis,photophysicochemical properties and DFT study

A new phthalocyanine-subphthalocyanine heterodyad ( 5 ) was prepared by Pd(0)-catalyzed Sonogashira coupling reaction between an asymmetrical phthalocyanine ( 3 ) bearing monoiodo and multiple triazolide moieties on its backbone and a subphthalocyanine ( 4 ) bearing axially propargyl group. The structure of this heterodyad ( 5 ) was subsequently confirmed by the conventional spectroscopic techniques. The photophysical and photochemical properties including; fluorescence and singlet oxygen generation of ( 5 ) along with its building chromophores ( 3 ) and ( 4 ) were also investigated. Interestingly, a purple colored solution was observed by this novel dyad which was significantly different from those colors (green or blue) obtained by phthalocyanine-subphthalocyanine conjugates. Based on steady state absorption spectroscopic data and transient absorption results, the synthesized dyad 5 was free of aggregation and there is good energy transfer occurs between Pc and subPc moieties. This result was confirmed using density functional theory (DFT) and time-dependent DFT (TDDFT) analyses: B3LYP exchange-correlation functional and the 6–31 + G(d) basis set.